When Gabe looks out the back windows of his home in Mount Pleasant, Michigan, he sees a quiet river winding through the trees. It's a far cry from the constant motion of the systems he's responsible for at Files.com - but the contrast is exactly what he was looking for.
"My rule has always been: my family gets everything they need first," he says. "Then I make sure all the systems are healthy and everyone at the company is unblocked. After that, I get as much done as I can."
That balance - real ownership at meaningful scale and the ability to design his life around family - is at the heart of Gabe's Files.com story.
Life Before Files.com
Before joining Files.com (then BrickFTP) in 2014, Gabe spent a little over a decade working for Central Michigan University, supporting the Housing and Dining department's technology.
"I was responsible for basically everything except networking - websites, databases, file servers, laptops, servers. It was a huge breadth of responsibility, and I learned a lot," he recalls.
The university environment gave him interesting problems and a decent technology budget, but there were clear limits:
- Compensation was capped in a typical public-sector way.
- Growth opportunities would require uprooting his family for another college town.
- There wasn't much room for intentional, entrepreneurial-style scaling.
At the same time, life outside of work had become more complex. He and his wife - who also worked at the university - were juggling two kids and a long list of medical appointments a couple of hours away in Detroit. The department was supportive and flexible, but the structure of the job wasn't.
"I remember thinking: why am I driving into an office 8 to 5 to talk to computers all day? I wanted to stay where I was, but do something bigger - and keep growing, financially and professionally."
That search led him to something still fairly novel at the time: a fully remote job posting for a small company called BrickFTP.
Choosing a Tiny Remote Startup in 2014
Back in 2014, 'fully remote' wasn't the default it is today. Gabe filtered specifically for remote roles - and BrickFTP popped up as one of three strong options he was considering.
"At first I thought, 'Who needs another Dropbox?'" he admits. "It just looked like another file-sharing company."
What changed his mind was the interview.
Kevin, Files.com's founder and CEO, personally interviewed Gabe. The company was still only a handful of people - but the conversation was unusually deep and technical.
"It was far more technical than any of the other companies I talked to. I walked away not totally sure I'd nailed every question, but really intrigued. Kevin was clearly an engineer, and I liked the idea of working for an engineer instead of just a generic manager."
The tech stack mapped neatly onto tools Gabe already knew, but the ambition was bigger. Even before he joined, the company was thinking about scale.
That mindset, and the chance to work fully remote from Michigan, tipped the balance.
Day One: "Is This Even Real?"
Gabe never met anyone in person before his first day. The entire process had been over the phone.
"Kevin even offered to fly his own plane out to Michigan to meet me," Gabe recalls. "My wife was like, 'Are you sure this isn't a scam?' A guy saying he'll fly his plane to come meet you for your remote job? It sounded unreal."
Gabe declined the visit - "If you have a plane and you're willing to do that, that's enough credibility for me" - and jumped in.
From the very beginning, it was a firehose.
Someone in a prototype version of his role had already laid groundwork using Chef and other tooling. Gabe spent his first week studying those scripts, understanding how servers were wired together, and learning how the system worked.
"At the end of the week he basically said, 'You got what you need?' I said 'Yeah, I think so,' and from there I just poked and tested and figured things out as I went."
What surprised him most was the complexity.
The company was already running multiple products on different platforms, with serious automation under the hood - things like managed certificates and early versions of the systems that still power Files.com today. It was all running on AWS at a time when cloud-native infrastructure was still relatively young.
"I'd never worked in the cloud at this scale. A lot of it felt crude - hand-tweaking scripts, manually picking IP addresses - considering how complicated the overall system was. It became clear very quickly that a big part of my job would be scaling the tooling to match the scale and ambition of the product."
The Firehose, By Design
Ask Gabe what working at Files.com feels like now, and he doesn't hesitate:
"It's still a firehose."
The difference is that the firehose has grown along with him.
"We're orders of magnitude more productive than I was in my old job with student employees," he says. "We ship dozens of times a day, across dozens of projects. You have to be comfortable juggling a lot, reprioritizing in real time, and getting thrown into projects where you're only vaguely familiar with the details."
That pace isn't for everyone - but for Gabe, it's energizing.
"I used to tell people: every day I encounter a problem I've never seen before, and if I do my job right, I'll never see it again. That still feels accurate."
Over the years, he's helped transform a small, scrappy product into a large-scale platform used by thousands of customers, building the infrastructure that keeps it all running.
One of his favorite projects: the self-signup custom IP feature.
"It's a very complicated feature," he explains. "It involves services running in multiple places, coordinating with each other, allocating real IP addresses in real time, wiring up the networking and routing, and then letting a customer click a button in the app and have traffic just start flowing through that IP."
When it all came together, it felt like magic - even to him.
"We can move IP addresses between servers and the customer never experiences downtime. The next time they connect, they're hitting a completely different machine and don't even know it. When I explain that to other engineers, they go, 'Okay, that's really cool.'"
Growing With the Company
When Gabe joined, Files.com was smaller and he thought the role might be simpler than wrangling a big university environment.
"It has shocked me how much the company has grown - and how much I've been able to grow with it," he says. "If you'd described my current job to me during the interview, I might have thought I was in the wrong interview."
For years, he was essentially the only person in his function. That forced him to constantly build better tooling, monitoring, and self-healing systems so a 'thin' infrastructure team could support a very large, very active platform.
Along the way, the scope of what he believes is possible has changed.
"There have been so many projects where I thought, 'I've never done this before, and I'm not sure I can,' and then we just figured it out. Do that enough times and your mindset shifts. You start thinking, 'I've never done that, but I guess I'll learn how now.' At this point, I feel like we can do just about anything technology-wise."
More recently, AI has further amplified what his team can tackle.
"There were projects we shelved for years because they were too big and gnarly. Now, with AI and better tooling on top of the systems we've already built, a lot of those ideas look a lot more feasible."
Life, Family, and a Steeper Curve
Over the 11 years Gabe has been at Files.com, his career and life have both changed significantly.
On the personal side:
- His wife has started and grown a successful small business (which uses Files.com).
- Their family has been able to travel to Europe and Central America.
- They've reached a level of financial independence he didn't expect back in 2014.
- They're approaching an 'empty nest' stage with wide-open options for what's next.
"The ability to even think about things like maybe moving to Europe or traveling most of the year feels mind-blowing compared to where I was when I started," he says.
Professionally, the trajectory is steeper.
"It's not that my growth suddenly became exponential, but the slope definitely changed," he explains. "Before, I felt constrained. To really advance, I'd have had to make big compromises - moving to a different city, changing environments completely. Here, there are more interesting problems, more opportunity to grow, and fewer reasons to compromise."
Equity ownership and the long-term potential of the company deepen that sense of ownership.
"There are hard days," he says. "But it's a lot easier to push through grungy, unglamorous work when you know you have real skin in the game - and when your own family's business is a customer."
What Future Teammates Should Know
If you're considering joining Files.com, especially on the engineering side, Gabe's advice is simple and direct:
- Expect the pace to be fast.
"This is not a let's schedule a meeting next week kind of environment. It's more, I'm going to solve this problem before lunch." - Expect to be overwhelmed at first.
"There's a lot of complexity in what we've built. Not just in what it does, but why it was designed that way. Getting into that headspace - understanding how all the pieces fit together - is the hardest and most important part of long-term success here." - Expect to learn constantly.
"If you like encountering new problems, building tools to solve them, and then never seeing that same problem again, you'll be happy here."
For Gabe, that combination - high-impact work at serious scale, real ownership, deep technical challenges, and the ability to build a life around his family in Michigan - has kept him engaged for more than a decade.
"I haven't looked for another job in 11 years," he says. "It's hard for me to imagine a place where I'd be more successful or able to achieve more than here."